There’s no sign of a life-changing surgery slowing Diva Jacqueline “Jackie” Dupree down. This week I had the opportunity to interview Jackie about her life, her struggles, and the profound foundation of friendships that she built in the New York Gay Football League (NYGFL). This flag-football organization was founded in 2004 and has become a pillar for the greater New York City LGBTQIA+ community.
I decided to join the league last year and it’s been one of the best decisions I made since I moved to New York. It was at the NYGFL 20th Anniversary party where I met Jackie. She was being honored with the Legacy Impact Award for her dedication to the league. That night she gathered the courage to perform for the first time since having her right leg amputated a few months ago.
“I’m not going to let me being in a wheelchair set me back… I still have a voice,” she said.
I was there in the crowd and watched her not only return to the spotlight but also witnessed a reunion with her chosen family.
It was truly a powerful and emotional moment. Jackie realized how much she needed her community as she glided towards the stage in her wheelchair and started singing Whitney Houston’s “Million Dollar Bill.”
“I felt like a real superstar,” Jackie said as she held back her tears. “They clocked to the stage because they missed me.”
Jackie’s return to the stage, however, was anything but easy. Her life changed forever last July when she scraped her foot on the corner steps inside a swimming pool. As a Type 2 diabetic, Jackie didn’t know that cuts and scrapes were considered serious injuries that needed immediate medical attention. By August, Jackie was admitted into the hospital after she noticed that her big toe started to turn purple. She spent several months in the hospital fighting off a super bug. That fight, ultimately, led doctors to amputate half of her right leg.
Jackie credits her family, friends, and the NYGFL for helping her overcome this life-altering moment.
“I call myself a true survivor, but thank goodness, I was with the football league… Y’all where there to help me survive,” she explained.
Jackie moved to New York in 1998 from Detroit to pursue a career as an entertainer. Her introduction to the NYGFL started in 2004 when she met Tim, one of its founding members. He was in the audience during one of her shows. Once it was over and Jackie was out of drag, she noticed Tim had been waiting for her. To this day, Jackie remembers the shock on Tim’s face when she reintroduced herself as the drag queen on stage since she “looked like a bouncer” without her make-up, heels, and wig. Although she had never played football before, Tim invited her to join to the league and she accepted.
With less than 50 players in the NYGFL at the time, Jackie helped recruit new members through her network in nightlife and asked the original owners of New York City’s gay bars if they’d be willing to sponsor the league. Not only was she the first open drag queen in the NYGFL, but Jackie was also one of the original hosts of the “Walk-Off,” which is a lip-sync drag competition that takes place every season.
After she was discharged from the hospital last December, Jackie moved back home to Detroit with her family to rest and adjust to a new normal. When she learned the NYGFL anniversary party was scheduled for March 2025, she was determined to go regardless of the few resources she had left. Jackie ended up buying a roundtrip ticket for nearly $400 and made her way back to New York with $20 left in her pocket.
As the crowd at Sony Hall yelled out “Jackie! Jackie! Jackie!” after singing “Killing Me Softly” by the Fugees, Jackie explained her feelings in that moment.
“I just needed to be there and I’m glad I did… it was so heartfelt and the way they received me was so well.”
Now that Jackie is rebuilding her life again, she is setting the stage for a future project. Her new mission is to inspire other performers who underwent similar struggles. Jackie hopes to host and organize a new drag competition that highlights handicapped entertainers. She says part of her new purpose is to help other handicapped or physically challenged performers feel the way she did that night at the NYGFL anniversary party.
“I’m not giving up my drag, I’m not giving up on Jackie,” she said.
